NCBI Taxonomy: 662921

Isodon nervosus (ncbi_taxid: 662921)

found 73 associated metabolites at species taxonomy rank level.

Ancestor: Isodon

Child Taxonomies: none taxonomy data.

Ursolic acid

(1S,2R,4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid

C30H48O3 (456.36032579999994)


Ursolic acid is a ubiquitous triterpenoid in plant kingdom, medicinal herbs, and is an integral part of the human diet. During the last decade over 700 research articles have been published on triterpenoids research, reflecting tremendous interest and progress in our understanding of these compounds. This included the isolation and purification of these tritepernoids from various plants and herbs, the chemical modifications to make more effective and water soluble derivatives, the pharmacological research on their beneficial effects, the toxicity studies, and the clinical use of these triterpenoids in various diseases including anticancer chemotherapies. Ursolic acid (UA), a pentacyclic triterpene acid, has been isolated from many kinds of medicinal plants, such as Eriobotrya japonica, Rosmarinns officinalis, Melaleuca leucadendron, Ocimum sanctum and Glechoma hederaceae. UA has been reported to produce antitumor activities and antioxidant activity, and is reported to have an antioxidant activity. UA may play an important role in regulating the apoptosis induced by high glucose presumably through scavenging of ROS (reactive oxygen species). It has been found recently that ursolic acid treatment affects growth and apoptosis in cancer cells. (PMID: 15994040, 17516235, 17213663). Ursolic acid is a pentacyclic triterpenoid that is urs-12-en-28-oic acid substituted by a beta-hydroxy group at position 3. It has a role as a plant metabolite and a geroprotector. It is a pentacyclic triterpenoid and a hydroxy monocarboxylic acid. It derives from a hydride of an ursane. Ursolic acid is a natural product found in Gladiolus italicus, Freziera, and other organisms with data available. Ursolic Acid is a pentacyclic triterpenoid found in various fruits, vegetables and medicinal herbs, with a variety of potential pharmacologic activities including anti-inflammatory, antioxidative, antiviral, serum lipid-lowering, and antineoplastic activities. Upon administration, ursolic acid may promote apoptosis and inhibit cancer cell proliferation through multiple mechanisms. This may include the regulation of mitochondrial function through various pathways including the ROCK/PTEN and p53 pathways, the suppression of the nuclear factor-kappa B (NF-kB) pathways, and the increase in caspase-3, caspase-8 and caspase-9 activities. See also: Holy basil leaf (part of); Jujube fruit (part of); Lagerstroemia speciosa leaf (part of). D018501 - Antirheumatic Agents > D000894 - Anti-Inflammatory Agents, Non-Steroidal > D016861 - Cyclooxygenase Inhibitors A pentacyclic triterpenoid that is urs-12-en-28-oic acid substituted by a beta-hydroxy group at position 3. C274 - Antineoplastic Agent > C129839 - Apoptotic Pathway-targeting Antineoplastic Agent Found in wax of apples, pears and other fruits. V. widely distributed in plants D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents D002491 - Central Nervous System Agents > D000700 - Analgesics C26170 - Protective Agent > C275 - Antioxidant D000893 - Anti-Inflammatory Agents D000890 - Anti-Infective Agents D000970 - Antineoplastic Agents D004791 - Enzyme Inhibitors 3-Epiursolic Acid is a triterpenoid that can be isolated from Eriobotrya japonica, acts as a competitive inhibitor of cathepsin L (IC50, 6.5 μM; Ki, 19.5 μM), with no obvious effect on cathepsin B[1]. 3-Epiursolic Acid is a triterpenoid that can be isolated from Eriobotrya japonica, acts as a competitive inhibitor of cathepsin L (IC50, 6.5 μM; Ki, 19.5 μM), with no obvious effect on cathepsin B[1]. Ursolic acid (Prunol) is a natural pentacyclic triterpenoid carboxylic acid, exerts anti-tumor effects and is an effective compound for cancer prevention and therapy. Ursolic acid (Prunol) is a natural pentacyclic triterpenoid carboxylic acid, exerts anti-tumor effects and is an effective compound for cancer prevention and therapy.

   

Oleanolic acid

(4aS,5S,6aS,6bR,8R,8aR,10S,12aR,12bR,14bS)-10-Hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydro-2H-picene-4a-carboxylic acid

C30H48O3 (456.36032579999994)


Oleanolic acid is a pentacyclic triterpene, found in the non-glyceride fraction of olive pomace oil (Olive pomace oil, also known as "orujo" olive oil, is a blend of refined-pomace oil and virgin olive oil, fit for human consumption). Pentacyclic triterpenes are natural compounds which are widely distributed in plants. These natural products have been demonstrated to possess anti-inflammatory properties. Triterpenoids have been reported to possess antioxidant properties, since they prevent lipid peroxidation and suppress superoxide anion generation. The triterpenes have a history of medicinal use in many Asian countries. Oleanolic acid exhibits both pro- and anti-inflammatory properties depending on chemical structure and dose and may be useful in modulating the immune response; further studies are required to confirm the immunomodulatory behaviour of this triterpenoid, and characterise the mechanisms underlying the biphasic nature of some aspects of the inflammatory response. Oleanolic acid is a ubiquitous triterpenoid in plant kingdom, medicinal herbs, and is an integral part of the human diet. During the last decade over 700 research articles have been published on triterpenoids research, reflecting tremendous interest and progress in our understanding of these compounds. This included the isolation and purification of these tritepernoids from various plants and herbs, the chemical modifications to make more effective and water soluble derivatives, the pharmacological research on their beneficial effects, the toxicity studies, and the clinical use of these triterpenoids in various diseases including anticancer chemotherapies. (PMID:17292619, 15522132, 15994040). Oleanolic acid is a pentacyclic triterpenoid that is olean-12-en-28-oic acid substituted by a beta-hydroxy group at position 3. It has a role as a plant metabolite. It is a pentacyclic triterpenoid and a hydroxy monocarboxylic acid. It is a conjugate acid of an oleanolate. It derives from a hydride of an oleanane. Oleanolic acid is a natural product found in Ophiopogon japonicus, Freziera, and other organisms with data available. A pentacyclic triterpene that occurs widely in many PLANTS as the free acid or the aglycone for many SAPONINS. It is biosynthesized from lupane. It can rearrange to the isomer, ursolic acid, or be oxidized to taraxasterol and amyrin. See also: Holy basil leaf (part of); Jujube fruit (part of); Paeonia lactiflora root (part of) ... View More ... Occurs as glycosides in cloves (Syzygium aromaticum), sugar beet (Beta vulgaris), olive leaves, etc. Very widely distributed aglycone A pentacyclic triterpenoid that is olean-12-en-28-oic acid substituted by a beta-hydroxy group at position 3. [Raw Data] CBA90_Oleanolic-acid_neg_50eV.txt [Raw Data] CBA90_Oleanolic-acid_neg_20eV.txt [Raw Data] CBA90_Oleanolic-acid_neg_10eV.txt [Raw Data] CBA90_Oleanolic-acid_neg_30eV.txt [Raw Data] CBA90_Oleanolic-acid_neg_40eV.txt Oleanolic acid (Caryophyllin) is a natural compound from plants with anti-tumor activities. Oleanolic acid (Caryophyllin) is a natural compound from plants with anti-tumor activities.

   

Dehydroabietic acid

(1R,4aS,10aR)-1,4a-dimethyl-7-(propan-2-yl)-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylic acid

C20H28O2 (300.2089188)


Dehydroabietic acid belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Dehydroabietic acid possesses antiviral activity[1]. Dehydroabietic acid possesses antiviral activity[1].

   

Dehydroabietic acid

InChI=1/C20H28O2/c1-13(2)14-6-8-16-15(12-14)7-9-17-19(16,3)10-5-11-20(17,4)18(21)22/h6,8,12-13,17H,5,7,9-11H2,1-4H3,(H,21,22)/t17-,19-,20-/m1/s

C20H28O2 (300.2089188)


Dehydroabietic acid is an abietane diterpenoid that is abieta-8,11,13-triene substituted at position 18 by a carboxy group. It has a role as a metabolite and an allergen. It is an abietane diterpenoid, a monocarboxylic acid and a carbotricyclic compound. It is functionally related to an abietic acid. It is a conjugate acid of a dehydroabietate. Dehydroabietic acid is a natural product found in Nostoc, Relhania corymbosa, and other organisms with data available. Dehydroabietic acid belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. An abietane diterpenoid that is abieta-8,11,13-triene substituted at position 18 by a carboxy group. Dehydroabietic acid possesses antiviral activity[1]. Dehydroabietic acid possesses antiviral activity[1].

   

Nodosin

(1S,4S,8R,9R,12S,13S,14R,16S)-9,14-dihydroxy-7,7-dimethyl-17-methylidene-3,10-dioxapentacyclo[14.2.1.0^{1,13.0^{4,12.0^{8,12]nonadecane-2,18-dione

C20H26O6 (362.17292960000003)


Nodosin is a delta-lactone. It has a role as a metabolite. Nodosin is a natural product found in Isodon oresbius, Isodon serra, and other organisms with data available. A natural product found in Isodon eriocalyx. 9,14-Dihydroxy-7,7-dimethyl-17-methylidene-3,10-dioxapentacyclo[14.2.1.01,13.04,12.08,12]nonadecane-2,18-dione is a natural product found in Isodon macrophyllus, Isodon japonicus, and other organisms with data available. Nodosin is a diterpenoid isolated from Isodon trichocarpus Kudo and I. Japonicus HARA[1].

   
   

Macrocalin A

(3R,3aR,6aS,8aS,11R,13aS,13bS)-3-hydroxy-4,4-dimethyl-10-methylenedecahydro-1H,8H-8a,11-methanocyclohepta[c]furo[3,4-e]chromene-8,9(10H)-dione

C20H26O5 (346.17801460000004)


Macrocalin A is a natural product found in Isodon serra, Isodon longitubus, and other organisms with data available.

   

Dehydroabietic acid

(+)-Dehydroabietic acid

C20H28O2 (300.2089188)


Origin: Plant; SubCategory_DNP: Diterpenoids, Abietane diterpenoids

   

Caryophyllin

(4aS,5S,6aS,6bR,8R,8aR,10S,12aR,12bR,14bS)-10-Hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydro-2H-picene-4a-carboxylic acid

C30H48O3 (456.36032579999994)


Oleanolic acid (Caryophyllin) is a natural compound from plants with anti-tumor activities. Oleanolic acid (Caryophyllin) is a natural compound from plants with anti-tumor activities.

   

Urson

(1S,2R,4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid

C30H48O3 (456.36032579999994)


D018501 - Antirheumatic Agents > D000894 - Anti-Inflammatory Agents, Non-Steroidal > D016861 - Cyclooxygenase Inhibitors C274 - Antineoplastic Agent > C129839 - Apoptotic Pathway-targeting Antineoplastic Agent D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents D002491 - Central Nervous System Agents > D000700 - Analgesics C26170 - Protective Agent > C275 - Antioxidant D000893 - Anti-Inflammatory Agents D000890 - Anti-Infective Agents D000970 - Antineoplastic Agents D004791 - Enzyme Inhibitors Ursolic acid (Prunol) is a natural pentacyclic triterpenoid carboxylic acid, exerts anti-tumor effects and is an effective compound for cancer prevention and therapy. Ursolic acid (Prunol) is a natural pentacyclic triterpenoid carboxylic acid, exerts anti-tumor effects and is an effective compound for cancer prevention and therapy.

   
   
   

(1s,4s,8r,9r,12s,13s,16r)-9-hydroxy-7,7-dimethyl-17-methylidene-3,10-dioxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁸,¹²]nonadecane-2,18-dione

(1s,4s,8r,9r,12s,13s,16r)-9-hydroxy-7,7-dimethyl-17-methylidene-3,10-dioxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁸,¹²]nonadecane-2,18-dione

C20H26O5 (346.17801460000004)


   

2,8-bis(acetyloxy)-6-hydroxy-5,5,9-trimethyl-14-methylidene-3,15-dioxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-11-yl acetate

2,8-bis(acetyloxy)-6-hydroxy-5,5,9-trimethyl-14-methylidene-3,15-dioxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-11-yl acetate

C26H34O9 (490.2202714)


   

(2r,4r,4as,4bs,5r,7s,10as)-4,5-dihydroxy-7-(3-hydroxyprop-1-en-2-yl)-1,1,4a-trimethyl-2,3,4,4b,5,6,7,10a-octahydrophenanthren-2-yl acetate

(2r,4r,4as,4bs,5r,7s,10as)-4,5-dihydroxy-7-(3-hydroxyprop-1-en-2-yl)-1,1,4a-trimethyl-2,3,4,4b,5,6,7,10a-octahydrophenanthren-2-yl acetate

C22H32O5 (376.2249622)


   

(1s,2s,3r,5s,7r,8s,9s,10s,11r,15s)-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecane-3,7,9,10,15-pentol

(1s,2s,3r,5s,7r,8s,9s,10s,11r,15s)-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecane-3,7,9,10,15-pentol

C20H30O6 (366.204228)


   

(1s,4s,8r,9r,12s,13s,14s,16s,18r)-14,18-dihydroxy-9-methoxy-7,7-dimethyl-17-methylidene-3,10-dioxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁸,¹²]nonadecan-2-one

(1s,4s,8r,9r,12s,13s,14s,16s,18r)-14,18-dihydroxy-9-methoxy-7,7-dimethyl-17-methylidene-3,10-dioxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁸,¹²]nonadecan-2-one

C21H30O6 (378.204228)


   

(1s,11s,12r,13s,16r,18r)-11,18-dihydroxy-6-methoxy-8,8-dimethyl-17-methylidene-3,5-dioxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁷,¹²]nonadecan-2-one

(1s,11s,12r,13s,16r,18r)-11,18-dihydroxy-6-methoxy-8,8-dimethyl-17-methylidene-3,5-dioxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁷,¹²]nonadecan-2-one

C21H30O6 (378.204228)


   

(1s,2s,4r,6s,8s,9r,10s,11s,13s,15r)-6-(acetyloxy)-8,11,15-trihydroxy-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-2-yl acetate

(1s,2s,4r,6s,8s,9r,10s,11s,13s,15r)-6-(acetyloxy)-8,11,15-trihydroxy-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-2-yl acetate

C24H36O7 (436.2460906)


   

2,8-bis(acetyloxy)-6,11,15-trihydroxy-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-3-yl acetate

2,8-bis(acetyloxy)-6,11,15-trihydroxy-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-3-yl acetate

C26H38O9 (494.25156979999997)


   

5,9,10-trihydroxy-12,12-dimethyl-6-methylidene-7-oxo-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-15-yl acetate

5,9,10-trihydroxy-12,12-dimethyl-6-methylidene-7-oxo-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-15-yl acetate

C22H30O7 (406.199143)


   

8-(acetyloxy)-3,6,11,15-tetrahydroxy-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-2-yl acetate

8-(acetyloxy)-3,6,11,15-tetrahydroxy-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-2-yl acetate

C24H36O8 (452.2410056)


   

2,11-bis(acetyloxy)-6,8-dihydroxy-5,5,9-trimethyl-14-methylidene-3-oxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-15-yl acetate

2,11-bis(acetyloxy)-6,8-dihydroxy-5,5,9-trimethyl-14-methylidene-3-oxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-15-yl acetate

C26H36O9 (492.2359206)


   

2,8-bis(acetyloxy)-3,6,15-trihydroxy-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-11-yl acetate

2,8-bis(acetyloxy)-3,6,15-trihydroxy-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-11-yl acetate

C26H38O9 (494.25156979999997)


   

(1s,7ar)-hexahydro-1h-pyrrolizin-1-ylmethyl 4-{[(2s,3r,4s,5s,6r)-3-{[(2s,3r,4r,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,5-bis(3-methylbut-2-en-1-yl)benzoate

(1s,7ar)-hexahydro-1h-pyrrolizin-1-ylmethyl 4-{[(2s,3r,4s,5s,6r)-3-{[(2s,3r,4r,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,5-bis(3-methylbut-2-en-1-yl)benzoate

C36H53NO12 (691.3567578)


   

9,10,15-trihydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-7-one

9,10,15-trihydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-7-one

C20H28O5 (348.1936638)


   

2,8-bis(acetyloxy)-6,15-dihydroxy-5,5,9-trimethyl-14-methylidene-3-oxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-11-yl acetate

2,8-bis(acetyloxy)-6,15-dihydroxy-5,5,9-trimethyl-14-methylidene-3-oxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-11-yl acetate

C26H36O9 (492.2359206)


   

(2r,3r,4s,5s,6r)-2-{[(4r,4ar,4br,5r,7s,8r,8ar,10ar)-7-ethenyl-5,8,8a-trihydroxy-1,1,4a,7-tetramethyl-decahydrophenanthren-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

(2r,3r,4s,5s,6r)-2-{[(4r,4ar,4br,5r,7s,8r,8ar,10ar)-7-ethenyl-5,8,8a-trihydroxy-1,1,4a,7-tetramethyl-decahydrophenanthren-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C26H44O9 (500.29851740000004)


   

14,18-dihydroxy-9-methoxy-7,7-dimethyl-17-methylidene-3,10-dioxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁸,¹²]nonadecan-2-one

14,18-dihydroxy-9-methoxy-7,7-dimethyl-17-methylidene-3,10-dioxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁸,¹²]nonadecan-2-one

C21H30O6 (378.204228)